Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada.
Bioorg Med Chem Lett. 2012 Feb 15;22(4):1719-21. doi: 10.1016/j.bmcl.2011.12.097. Epub 2011 Dec 30.
The β-d-galactosyl-(1,3)-α-N-acetyl-d-galactosamine disaccharide is present in antifreeze glycoproteins (AFGPs). Analogs of this disaccharide including the β-linked (1,3)-, (1,4)-, and (1,6)-galactosyl-N-acetyl galactosamine and the β-(1,3)-galactosyl-galactoside were synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The results from this study demonstrate that the β-linked-(1,4) disaccharide exhibits more potent IRI activity than the native β-linked-(1,3) disaccharide. The C2 N-acetyl group of the disaccharide does not affect IRI activity but in monosaccharides, the presence of the C2 N-acetyl group decreases IRI activity. The current study will facilitate the design of potent small-molecule ice recrystallization inhibitors.
β-d-半乳糖基-(1,3)-α-N-乙酰-d-半乳糖胺二糖存在于抗冻蛋白 (AFGPs) 中。该二糖的类似物包括β-连接的(1,3)-、(1,4)-和(1,6)-半乳糖基-N-乙酰半乳糖胺以及β-(1,3)-半乳糖基半乳糖苷，它们被合成并评估了其对冰晶重结晶抑制 (IRI) 的活性。这项研究的结果表明，β-连接的-(1,4)二糖比天然的β-连接的-(1,3)二糖具有更强的 IRI 活性。二糖的 C2 N-乙酰基不影响 IRI 活性，但在单糖中，C2 N-乙酰基的存在会降低 IRI 活性。本研究将有助于设计有效的小分子冰晶重结晶抑制剂。
